


Sorry Officer!

by slaughterme



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Blow Jobs, Dubious Consent, Felching, M/M, Outside Sex, Panties, Police Officer Derek, Rimming, Stiles Stilinski in Panties, cross dressing
Language: English
Status: Completed
Published: 2015-07-15
Updated: 2015-07-15
Packaged: 2018-04-09 11:47:51
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 1,965
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4347410
Author URL: https://archiveofourown.org/users/slaughterme/pseuds/slaughterme
Summary: <blockquote class="userstuff">
              <p>Stiles leaves the drag queens at the bar when he spots one of his dad's deputies and runs into some trouble in the woods.<br/>Stiles never knew wearing girl clothes and panties could be such a turn on.</p>
            </blockquote>





	Sorry Officer!

**Author's Note:**

> Sorry for all the fails spotted throughout, I broke three fingers due to an ice skating fail and it's late. I'm too lazy to proof read.

Stiles doesn’t even remember how he ended up here.

In high school Stiles was obsessed with Lydia and how she looked. He loved her clothes, her shoes and her hair but he felt no sexual attraction to her or any other girl. It took him a while but he figured out why a month ago. 

He wants to wear girl clothes. 

It freaked him out for a while before he bit the bullet and did a quick google search which led him to xdress.com who sold male lingerie. He debated for a solid hour before he ordered a Lolita princess dress, a tartan garter skirt and black and pink lace panties. The total cost was around $200 which made Stiles wince as he typed in his credit card details.

The rocked up a week later and Stiles didn’t get to the door in time, he was at his part time job at a pizzeria a couple streets over. His dad got to the package first, then proceeded to freak out over the silk and lace before he closed the box, stared at Stiles’ name long and hard before he placed the box on his son’s bed.

It was an awkward conversation when Stiles got home and the Sheriff wished his wife was still alive, she would have known how to deal with this.

Stiles got into the habit of wearing the panties and garter skirt when he was home alone and had put the dress on a few times but decided they needed matching socks and high heels. He drove two towns over and went on a shopping spree in attempts to find what he needed. He ended up with a pair a thin , light pink thigh high socks with black bows and black high heels.

It took a while for him to learn to walk in them. Then he had to wax, which ow.

Tonight he decided to sneak into the Jungle wearing the whole get up, the garter skirt hidden under the dress. He didn’t have a wig but he had shaggy hair. He was quickly taken under the drag queens’ wings and a short brown wig found its way onto his head and before he knew it, he had a soft layer of makeup on. They got as far as pink lips and black eyeliner before the head queen decided he looked decent.

“You look so pretty sweetie! If you weren’t such a twink I’d go after you myself!” She exclaimed, patting Stiles’ cheek.

Somehow that led to Stiles walking around in the woods. Why? Because Stiles saw one of his dad’s deputies walk into the bar so Stiles ran for it, out the door and into the woods and now he was lost.

He was careful in making sure nothing caught on his dress, he was not letting a $100 dress die due to him being clumsy. A hand grabbed his shoulder and a voice growled “this is private property of the Hale family. What would you dad think if he knew you were here.”

Stiles froze. Oh God no, not Deputy Hale! Derek Hale was a scowling brute of a man who has had it out for him since his first day on the force where Stiles accidentally split coffee on the man on his way to his dad’s office. He tried baking for the man, he acted as polite as he could but nothing seemed to work on the older man. He’d just growl for Stiles to go away before outright ignoring him. Why did Stiles think it was a good idea to go to the Jungle dressed as a girl for his 18th? Oh right, he has no friends because everyone thinks he’s weird!

Stiles turned around, pulling the wig off so he had something to fumble between his fingers, “look, can we just forget this happened? I didn’t mean to get lost but I did trying to get away from you! I don’t want to be seen like this by anyone my dad works with or I personally know. So show me how to get out and I’ll ge-“ Stiles was cut off by Derek shoving him to the ground.

Stiles’ knees hit the clearings floor with a painful thud making the boy whine in pain. He looked up at Deputy Hale in confusion, “Wha-“ Stiles started before he was cut off by Derek.

“I can think of a few things you can do to make me not tell anyone about your little kink. We don’t have to if you don’t want to though, I’ll drop it and we’ll never even bring it up, or you can suck my cock and we can see where it goes from there,” Derek stated, looking down at the pretty boy.

Stiles’ licked his lips and looked at Derek’s crotch with hungry eyes. It was no secret to Beacon Hills Sheriff’s department that Stiles had a crush on Deputy Hale. Everyone could see how hard Stiles tried to win back the man’s trust and how bad he wanted the older man’s affections. 

 

Derek smiled down at the twink before unzipping the fly on his uniform pants. Stiles groaned when Derek’s hard cock sprang free, the older man was not wearing underwear and that made Stiles leak into his lace panties. The younger boy couldn’t help himself, he lent forward and licked over the man’s sensitive head, lapping at the precum pooling at the slit. His eyes fluttered closed, he sealed his lips around the older man’s cock head, moaning as he sucked, wanting more of that salty sweet.

The older man began to slowly thrust into his mouth, pushing his cock deeper every second thrust, forcing himself into Stiles’ mouth. The younger just moaned around the thick cock, tongue running along the thick blue vein on the underside of the man’s cock.

Stiles hollowed his cheeks and sucked harder causing Derek to thrust down hard, plunging down Stiles’ throat, making the younger’s eyes water and throat constrict around his cock as he gasped for air. Derek fucked his throat hard with a couple more thrusts before pulling out, leaving Stiles blissed out. He held his cock a few centimeters away from the younger’s lips, still connected to the boy in a thick rope of saliva. 

“Come on bitch, get on the table. Face down, ass up,” Derek ordered, pointing to one of the picnic tables in the dark clearing.

Stiles scrambled up, slipping in his heels and almost falling over, Derek having to catch the younger to steady him before pushing the boy gently towards one of the tables. The boy rushed over, slipping a bit in his heels before he lent on the table, pulling his dress up and off. He folded the dress carefully and sat it on one of the seats before getting into position. Derek watched the boy do this and licked his lips at the sight of the pretty pink socks being held up by the black straps from the garter skirt.

He walked up behind the younger boy, running his hands up his sock clad legs, rubbing the skin on show, pausing to rub the boys butt cheeks. The pretty black trimmed pink panties almost sitting like a g-string due to Stiles’ bubble butt. “God, you’re so pretty baby, you were made for me. I’m going to ruin your innocence and you’re going to let me because you’re fucking desperate for cock, not just any cock though, no, you want my cock. You want my cock filling you up, plugging my cum deep inside you and ruining you for anyone else. You’ll be mine forever because I’m going to need more than just a taste sweetie,” Derek growled, pulling the lace panties to the side so he could see the younger’s pretty pink hole.

The deputy couldn’t help himself, he lent down and licked a large, wet stripe up Stiles’ hole making the boy shudder and gasp out tiny ‘please’s as he humps his hips backwards, wanting Derek to do it again. Who was Derek to deny such a pretty little thing? Derek lapped forwards against, getting the younger’s hole nice and wet before sliding a finger in along his tongue.

The younger boy moans loudly and thrusts hard against the finger and tongue. Derek smiles against the boy’s hole and slides another finger in, making the boy mewl and push back, arching his back into it which makes his skirt lift higher.

Derek stretched the boy for a little longer, scissoring his fingers in and out of the boy’s hole before sliding a third finger in alongside of them. Derek held the boy’s ass open with one hand as he watched his fingers slide in and out of the pretty pink hole before he pulled them out, chuckling at the boy’s distressed whine and hip shifting.

Derek stands up at full height, his dick hanging from the zip of his pants, before pressing his groin against Stiles’ ass, his thick cock sliding between the boy’s cheeks as he fixes Stiles’ garter skirt to hide his own groin. “Such a good little bitch, and you’re all mine,” He growls out before slamming his hips, his cock catching on Stiles’ hole a couple times before he slides all the way in.

Stiles lets out a loud wail, shoving his face against the wooden table, his hips twitching uselessly back onto the deputy’s thick cock. The older man grabbed onto the boy’s hips, forcing him to hold still and he adjusted on Derek’s cock.

Derek ran his nails down Stiles’ back as he waited, leaving thick red marks and speckles of blood to coat the boy’s skin. After a couple of minutes Stiles began to slowly shift his hips back and it was all over for Derek’s resistance. The older man grabbed onto the boys hips and fucked up hard into him, pulling the boy around on his cock. He thrusted up into the boy, pulling him down harshly onto his cock, brushing against his prostate and making the boy scream.

They kept this pace, Stiles being jerked back and forth on Derek’s thick cock, the picnic table wood scratching painfully against his naked chest. Derek was brutally pounding into the boy’s prostate with every second or third thrust, driving the boy wild and making wanton gasps and moans in a constant stream.

It didn’t take long until Stiles started jerking and rolling his hips, rubbing his dick against the soft lace. The pressure and movement made Derek moan, thrusting harder into the boy to chase his release. Stiles came first, eyes rolling in his head, back arching, filling his pretty panties with cum and clamping down on Derek’s cock.

Derek followed soon after, biting down on Stiles neck until his mouth filled with blood, the boy moaning and clamping back down onto his cock as he pumped his seed into the boy. They stayed like that for a while, Derek’s dick resting inside the boy’s abused hole before the older man slowly pulled out making the younger whine in distress as cum leaked out of his hole.

Derek stilled for a second, watching it slide from the boys hole before he swooped down, catching as much cum as he could before grabbing Stiles’ shoulder and hauling the boy up. Derek forced his lips onto the boy who just mewled and licked into his mouth, chasing the taste of Derek’s cum.

Derek pulled back and smiled at the boy. “Let’s get out of here. I finished shift an hour ago and was on my way home when I saw you. How about you come with me?” Derek asked, winking at the boy.

Stiles’ couldn’t have jumped off the table and have put his clothes on faster.


End file.
